Introspections
by singersongwriter
Summary: A collection of short insights into what the characters could have been thinking in some of my favorite moments from the show.
1. A Missing Necklace

_The idea of this collection of stories is to delve a little into what the characters may have been thinking in some of our favorite SSD moments. Each chapter is a different moment and isn't in any particular order. They'll be super short, but let me know what you think._

 _I don't own SSD. I wish I did. That would be awesome._

Shane's look of worry was evident immediately as she placed her hand at her neck where her necklace was supposed to be. Oliver attempted to reassure her that they would find it. He may not have known the full story behind the necklace, but he knew how important it was to her. He'd never seen her without it.

Just as Oliver was about to coordinate the search, Jordan approached rather unexpectedly. Oliver got that distinctly annoyed feeling in the pit of his stomach again. He wasn't a fan of this guy.

"Did you lose something?" Jordan asked.

Oliver needed to help despite Jordan's arrival. Shane was getting distressed, so he turned his attention to the task at hand. "Yes. Ms. McInerney misplaced her necklace. It's a small...gold disc with a purple...crystal bead."

Oliver found himself pausing slightly as he described the necklace he had seen her wear so many times, and his extremely accurate description caused Shane to pause and find his eyes for just a moment. She couldn't help but be surprised at his knowledge and the look she threw him suggested so.

Oliver could do nothing in that moment but nod slightly - almost imperceptibly. Of course he knew what the necklace looked like. He knew almost every inch of her. It was just as much a part of her as her beautiful smile or her flowing blonde hair. This was one of those small moments that passed between them often. One that suggested that they knew each other on a much deeper level than either was ready to admit fully. That would have to wait for another day.


	2. Letters from the Past & Present

_Second chapter...another of my favorite moments. Feedback is useful, so please review and let me know what you think. As always, I don't own SSD or these characters._

"Better yet. Read them out loud. Together."

Oliver couldn't help but glance towards Shane when he said that last word. The secret to true love had indeed been found in those letters. Katherine and Jonathan had shared their hearts and souls with each other on those pieces of paper over 100 years prior. Yet somehow, their words had rung as true in that locked bank vault for the two strangers in time that read them as they had the day they were written.

As Oliver and Shane shared another one of those connecting moments - the ones that seemed to knit their hearts and souls closer together - he realized there was something nice about being able to read the words from the letter aloud to her. It was as if he was given the opportunity to say the things his heart felt but that his mind was still struggling to grasp.

All he knew was that the letter he had written himself in that vault was not the same as the ones he had read with Shane, and he couldn't imagine himself sharing Jonathan and Katherine's words with Holly. The realization struck him deeply, and he once again forced himself to focus on the work of delivering the mail.

He would mail his letter. He would be willing to try again if Holly read his words and chose to return. That was the right thing to do. But each of those moments with Shane was making it harder for him to keep from wondering what it would be like to be free to use his own words to tell Shane what she was beginning to mean to him.


	3. What's in a Name?

_These are three separate moments from the Christmas movie, but they were all connected. It's my version of Oliver's mindset during those times._

Jordan recognized an opportunity when he saw one. "I noticed you call Rita, 'Rita,' but you call Shane 'Ms. McInerney'?"

"Yes, well, it started as an office formality, and I just continued. I don't really know why I do that."

"I think you do."

Jordan walked away leaving Oliver to contemplate what he meant.

Why did he call her that? He remembered for a moment that first day in the DLO when he first refused to call her by her given name. It became a bit of a game - initialling calling her a different name entirely and then just using the more formal Ms. McInerney. Eventually it had become a habit. Comfortable. That was who she was. He only called her by her first name when he really needed to get her attention or tell her something important - explaining about her dad's letter, comforting her in the bank vault. He only called her by her first name when - it was then that it clicked. He called her Shane when things crossed from professional to personal.

He called her Shane in those moments when he really wanted to connect with her...to help her. And those moments, few as they were, held great meaning. It was if speaking her first name somehow knit them closer together, and that wasn't a wise thing to do. It opened a window into feelings that could not be contemplated let alone explored. No. He had to call her Ms. McInerney. He had to keep that wall up to prevent her from moving further into his heart than she had already.

Ms. McInerney wasn't listening to him. She was hurt and confused, and walking away. Oliver did the first thing that came to mind. The one thing he felt would get her to turn around and face him.

"Shane!"

She stopped instantly. "What did you just call me?"

Oliver didn't stop to think about the consequences of using that name. He knew only that he finally had her attention, and that he had a message she needed to hear. It was a message of hope and love and forgiveness and holding firm in a storm. As often happened though, the use of her name broke down those artificial barriers he had built up between them. He moved closer to her than he had since that day in the vault. He basically told her that he believed God had put him in her life for a reason. He felt his heart constrict when she placed that kiss on his cheek and laid her hand on his chest. He had done it. He had helped her find peace. As he stood there looking at the empty envelope, though, he realized that he had once again crossed that boundary. It happened every time he said her first name, and he would need to once again build that fence - even though it was becoming more and more clear to him that it was an imaginary one.

After the pageant, they stood together in the moonlight talking of the day and joking about the bear. As the conversation closed, he made sure to address her as Ms. McInerney - but as he said it his voice could not maintain a completely professional or distant tone. The name flowed as more of a term of endearment than an office formality. Using her first name may have been the catalyst to break down the barrier between them, but now that it was crumbling, it didn't matter what name came from his lips when he spoke to her, his eyes would betray his true feelings.


	4. Building a Porch Swing

_Ok - so I'm not sure this really belongs in this collection, but I'm putting it here anyway. I've often wondered about this little exchange in FPWL:_

 _Shane: "How long have you been here?"_

 _Oliver: "An hour and a half. Would have been less, but I had to stop and explain to a couple police officers why I was installing a porch swing at 2 am."_

 _Yeah - Oliver with the police officers would have been a great scene to see in the film. Here's my super short version of how that conversation could have gone. As always, I don't own Signed, Sealed, Delivered or any of the characters. I just like to pretend I do sometimes._

Oliver crouched on the porch beneath the swing attempting to reach a particularly difficult bolt.

"Sir, is everything alright here?" Oliver was startled by the voice and turned quickly to see the two officers who were eyeing him suspiciously.

"Uhhh...yes," Oliver answered as he hastened to stand up. "I'm just….ummm...building this..." Oliver gestured toward the half-completed swing.

"I can see that," responded the officer. "Any particular reason why you chose to build a porch swing at 2 o'clock in the morning?"

Oliver wasn't sure what to say in response to that question. When he had left the Mailbox Grille earlier, it was simply the only thing he could think of doing. The idea of buying the swing had actually come to him the minute Shane had told him the story from her childhood at the ribbon-cutting ceremony, but Shane's subsequent revelation and Holly's appearance had pushed it from his mind. Something about knowing his marriage was officially over had brought the idea front and center again, and he hadn't really thought about why it was something that had to be done now.

The officers were clearly annoyed at his hesitation and took a step forward. Oliver offered the first excuse that came to his mind.

"Well uhhh, officer, my friend's birthday is Monday, and I thought I would surprise her with this as a gift."

"Your friend?" the officer glanced toward his partner with a hint of a smile. Oliver completely missed the emphasis the officer had placed on the word "friend."

"Yes. She lives here but is out for the evening with some colleagues from work. I thought perhaps I could have it completed by the time she returns home." Oliver finished the sentence confident enough that it sounded plausible.

"Well. Try to keep it down so you don't disturb the neighbors, and good luck finishing before she gets home. You should certainly score some points for something like this." The officer motioned to his partner to follow him, and they headed back down the walk towards their car.

Oliver knelt back down in front of the swing to continue tightening the bolt he had been working on when they arrived. He didn't have time to think anymore about the conversation or even wonder for sure about what he was really doing there at this hour. He needed to get to work. As he placed his left hand on the ground to steady himself he heard a soft thud and glanced down at his wedding ring. He quickly slipped the band off his finger, placed it in his pocket and set to work again with a sense of peace he hadn't felt in the longest time.


	5. A Call for Support

_I got a couple requests to continue this little experiment, so I thought I would post a new chapter. I really love Truth Be Told. It may be my favorite. Oliver spends so much of the movie on the cusp of asking for Shane's help - and the one time he does ask, we don't get to hear it._ _Here's how that could have happened._

 _(PS - I don't own SSD...but then you probably knew that.)_

Oliver walked out of the park and away from his father as quickly as he could. Of course the man he was leaving in the park wasn't really his father after all. That other man was. He repeated the words he had said earlier in his head. Knave. Scoundrel. The thoughts were coming faster than Oliver could process them. It was becoming a familiar feeling - the world collapsing around him.

Holly had returned less than a week ago. He remembered walking into work last Friday morning with much the same feeling as he had now - confused, lost, not quite sure what to do with himself. And then he heard that voice.

" _Going my way?"_

He looked up to see Shane smiling down at him, and then she asked him to join her on the platform. They talked - about snowmen, and forgiveness, and doing the right thing. She was surprisingly good at making him feel better...feel hopeful that there could be a resolution to the mess in which he was currently mired. He could use some of that encouragement now - that peace that she brought him with just her presence and her smile.

He knew he shouldn't ask. He had fought off the urge to ask her to stay earlier at the park because this - possibility - of the two of them as more than colleagues was still too new. He had already pushed a little too far too soon by purchasing the porch swing - something he had realized when talking to Norman on Monday. But, dear Lord, he needed her right now. He needed someone who he trusted would be on his side.

Oliver's presence at the lawyer's office almost startled him. He wasn't quite sure how he had gotten there, the thoughts of his current situation had so clouded his mind. He walked into the brightly lit office and glanced at the large glass clock that hung on the wall. 1:30. He realized she could be there before the meeting started if he called now. Perhaps it was the need to act immediately if he wanted her with him that spurred him on, but he walked directly to the receptionist and requested use of the phone. Shane's voice on the other end immediately calmed him some.

" _Oliver O'Toole's office._ "

"Miss McInerney, things took a rather unexpected turn after I last saw you in the park, and I could benefit greatly from your assistance if you aren't too busy at the DLO."

" _Where are you?"_

"The lawyer's office. I believe you have the address. You gave it to me earlier."

"Of course. I'll be right there."

Oliver hung up the phone, thanked the receptionist and found a seat. His thoughts went back to his current situation. His father. Fathers. The past truly had changed in the blink of an eye. He glanced at his pocket watch, closed his eyes momentarily, and waited for her arrival.


	6. And So It Ends

_I've had the idea of tackling this scene for a while. Nothing earth shattering here obviously. I think we all know by now what caused Oliver to end the dance. This perhaps just puts all of the reasons and feelings in one place._

 _I don't own SSD or it's characters._

"Good-night."

Oliver didn't stop to listen for a reply, although he would have heard a "goodnight" in return if he had. He clutched his jacket and walked out of the DLO as quickly as he could. He needed some air.

Things had gotten out of hand. He had been enjoying the dance lessons with Ms. McInerney, and everything had been fairly straightforward until tonight. She was his colleague, and they were friendly but not necessarily friends. He had asked her to be his dance partner because he felt she was a capable person. He didn't doubt her ability to step in on short notice and learn all the steps before the showcase. Yes, he had enjoyed spending some additional time with her outside of work. She was different. Intriguing. And dancing with her had been almost fun even. She made him smile, and he could tell there was the possibility that the two of them could eventually become friends. But tonight had changed all that.

Perhaps it was the song she chose. Billy Joel really was a perfect balance between his classical tastes and her more contemporary vibe. "Same tempo, same steps," she had said, and he couldn't help but smirk a bit as he offered her his hand. They really had found a rhythm together, and the more relaxed music and atmosphere caused him to let his guard down a bit. Oliver, perhaps for the first time, truly let the music tell him where to go, and they reached a point in the song where it just made sense to pull her closer to him - and then everything started to unravel. He got lost. In the dance. In her eyes. In the moment. And when he pulled her slowly out of the dip, he knew he had never felt quite like that before. Like he was exactly where he should be and like he was with exactly the right person.

Except she was the wrong person. He was married, and this - whatever this was - was wrong. He had quickly let go of her hand and stepped away to turn off the record player. Now he was out of there, and he could breathe a little better. But he was distraught. He had taken the dance lessons for Holly - to prove to her that he was willing to do something that she liked, but everything had backfired.

Oliver knew he couldn't dance with Ms. McInerney again - especially not at the showcase. He could only imagine what tonight's dance would have looked like had someone seen them together. He certainly didn't look like someone awaiting the return of his wife, and to be honest with himself, he hadn't felt like someone doing that either. No. This was a mistake and one he must rectify as soon as possible. He would tell her tomorrow. It was the right thing to do. He knew that...and he also knew he would have to push away the nagging disappointment that crept into his heart at the thought of never dancing with her again.


	7. Outside the Church

_I almost always tackle Oliver's point of view, because I feel like I understand him a little better. This is less of a story and more my attempt to try to figure out what's going on in Shane's head. She is such a complicated character - strong, yet vulnerable in so many ways. Anyway - here's my take on Shane's thoughts just before she walked into the church in From the Heart._

"It's been a long time since we danced."

Shane read the last line again as she sat in the driver's seat of Oliver's car looking at the church building. The emotions hit her once again just as they had when she first read the words aloud to Norman.

"Over a year," she said to herself.

She wasn't entirely sure what this invitation meant. She was excited to receive it - especially since her initial confidence in Oliver's interest in her after he purchased the porch swing had faltered over the last few months. He had taken a step forward with the dinner invitation in Washington, but when they returned things had gone back to normal. Other than the occasional glances (that at this point she felt could mean anything) he had given her no indication that he wanted to test the waters.

To be honest, Shane had been a little annoyed with herself over the past few months. She had fallen for Oliver a long time ago. Though she got a glimpse of his charm during that very first dance to "Moon River," it was the strength and compassion that he showed those they helped that endeared him to her over time. She knew she wanted something more from their friendship, but she just hadn't found the courage to say anything. That wasn't really like her, which was the source of her frustration with herself. What had Steve said? He always knew where he stood with her. She had not been that forthcoming with Oliver, and it bothered her.

Why couldn't she just come out and tell him that she was interested? Why hadn't she asked him out? The opportunity had certainly presented itself on numerous occasions. She had been telling herself that it was her respect for Oliver and the things he had endured that kept her silent and waiting for him to make a move. She told herself that he wasn't ready yet - she even told Rita that same story a couple days prior. Deep down, though, she knew that her hesitation had less to do with her protecting Oliver's feelings and more to do with her attempt to protect her own.

She was scared of being hurt again. She had been abandoned by her father, and her relationship with Steve had been pretty one-sided. She had wanted so badly for it to work out, but the more she poured into it, the further away he seemed to get. Shane couldn't bear the thought of that happening with Oliver. She knew if she waited for him to make the move then she could protect herself from the vulnerability of showing her feelings first. But something in her knew that wasn't the way she should live. Life is short, after all, and sitting on the sidelines waiting for things to happen for you is a waste of time.

Shane took a deep breath and slid the card back into her purse. Hopefully this invitation meant what she wanted it to mean. Either way, though, she vowed to herself that if Oliver was still willing to go to dinner that she would be more assertive in her attempts to find out his true feelings and would be more open about her own. It was time to stop living in limbo and start living her life.

Shane walked into the church with a sense of purpose and felt an involuntary smile creep up on her lips as she heard the choir finishing the last notes of practice. The sight of Oliver made the smile widen for just a moment - before the redhead he was with made it disappear for good. The resolve she had felt just moments prior was replaced with fear and timidness and that all-too-familiar urge to run away.


	8. A Valentine Introspection

_My Valentine's Challenge entry - in the form of another chapter in the long abandoned "Introspections" series. The future for our beloved couple is too confusing for me to speculate, so I decided to go analyze the past instead. It echoes some of what I wrote in the last chapter of this series, but I think it's true to Shane's mindset at the time._

* * *

Just a made up holiday to sell chocolates and pressure men into taking you to a romantic restaurant and tell you they can't live without you. Yes, it was a bleak assessment of Valentine's Day as Oliver had put it, but it was the correct one. Shane's walk home after being sent from the Mailbox Grille to go relax and putter was one of quiet reflection. She had allowed herself to get her hopes up a bit about this Valentine's Day, although at this moment she wasn't sure why. She remembered the events of the past year vividly. There were so many moments between Oliver and her that had led her to believe that they were on their way to something…well, at least on their way to TRYING something. But nothing had happened. He had offered to take her to dinner in DC and bought her the lot to rebuild her childhood home - things that seemed to indicate that things were moving towards a relationship outside of work. Then they got back to Denver, and...nothing. She didn't get it. His divorce was finalized. There was nothing standing in their way anymore. The only logical conclusion was that he just wasn't actually interested.

That last thought struck a cord unexpectedly, and a hot tear slid down her cold cheek. She loved him. And he didn't feel the same way. She wondered how he would actually be spending his Valentine's Day. Maybe he had someone else in mind? He _had_ been evasive about revealing his plans when she had asked.

Her thoughts were interrupted as she approached her house and saw Rita on the sidewalk in front of her. Shane briefly wished her excuse to be alone on Valentine's was because she had been whisked off to work in DC rather than because the man she loved didn't share her feelings. She pushed those thoughts aside, however, to greet Rita in her typical Shane fashion. Upbeat and confident. That was the trick...although being given a box of decorations for a Valentine's party for people without dates was certainly salt in the wound. The walk up the steps to her porch had never seemed longer. She dropped the wretched box on the porch swing that had once held so much promise to her and went to unlock her door when Oliver's voice popped into her head.

"Check your mail."

So she did. And there was nothing. Again.

"Figures."

* * *

Just realized I forgot the "surprise" element. :) Surprise! It wasn't a happy story! lol


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